Jim Messina, the former campaign manager to President Barack Obama who spent two decades in politics out of the public eye, is increasingly stepping out from the shadows — and onto other Democrats’ toes.

Messina is moving aggressively to capitalize on his newfound fame and status as the maestro who ran a masterful reelection campaign for a president mired in a slumping economy. He’s building a political fiefdom through his deep ties to rich Democrats and a nexus of big-money operations including the Obama nonprofit Organizing for Action, whose major donors Messina is hosting in his office Monday and whom the president will address Tuesday, and Priorities USA, the pro-Obama turned pro-Hillary Clinton super PAC.

He’s grabbing clients around the world, some of whom seem at odds with one another. And he’s grabbing cash, in the form of speeches at roughly $50,000 a pop to corporate special interests like the American Petroleum Institute and foreign groups like the government of the United Arab Emirate of Sharjah whose positions don’t always jibe with liberal or democratic ideals.

It’s the first time that Messina, 44, a former Hill staffer raised by a single mother on a tight budget, is making serious money. He appears to be following a path paved by George W. Bush’s political guru, Karl Rove, who turned his master strategist role into a vaunted brand and created a shadow version of the Republican Party machinery through his unlimited-money Crossroads groups.

But Messina’s effort to tap his earning potential while maintaining a hand on the levers of the party’s apparatuses has fueled grumbles from various Democratic donors and operatives, who accuse him — privately, and without the risk or accountability that can come from on-the-record criticism — of taking more than his share of the credit for a multifaceted victory, and of a cash binge that exposes Obama and former Secretary of State Hillary Clinton to potential backlash. Some Democrats question whether it’s unwise to have a single figure wield so much influence, while many former colleagues see Messina less as a Rove-like figure than as a deft operator who successfully implemented a strategy crafted by others.

Messina’s allies cast him as a reluctant participant in the new big-money political world and argue he’s taking a leadership role only because it’s important for someone with wide experience and respect to help prepare the party for a potentially tricky post-Obama transition.

“It’s a lot to put on someone’s shoulders, but we need a Karl Rove-type figure, and Messina has a large Rolodex. Or iPad,” said Donna Brazile, who chose a more conventional path after running Al Gore’s 2000 presidential campaign, becoming a pundit, corporate consultant and strategist emeritus of sorts.

“I see Karl Rove as kind of Boss Hogg. And I see Messina as the consigliere — the quiet guy,” said Florida lawyer John Morgan, a Clinton intimate who became close to Messina during the 2012 campaign and donated at least $50,000 to OFA afterward. “The real difference is one has an outsized ego and it’s about him, and the other has an ego that’s very much in check and it’s about the cause and the candidates.”

Messina — like Rove before him — has gravitated away from the party and campaign system in which he cut his teeth toward the unlimited-money outside infrastructure that reshaped politics after the Supreme Court’s 2010 Citizens United v. FEC decision. It’s a notable shift, given that Democrats up to and including Obama had assailed Rove and the big money he was raising as everything that’s wrong with modern politics, before finally coming to embrace the new reality in which money and power have migrated to the outside groups and away from the party and campaign system.

Recently, Messina began quietly backing away from the inside system, last month ending a $15,000-a-month consulting agreement with the Democratic National Committee. The move came as he assumed leadership of the pro-Clinton Priorities USA outside spending outfit, prompting legal and practical questions about the many hats he was wearing. “Obviously, respecting both the letter and the spirit of the law, he just couldn’t have done both,” said a source close to Messina. The source added that Messina was also preparing to end a $7,000-a-month contract with Obama’s still-idling presidential campaign because he had mostly finished the work of winding it down.

Yet it’s Messina’s pursuit of new opportunities that has caused the most sniping from anonymous Democrats. One former Obama adviser, who asked not to be identified, said “there’s a freneticism” to it. “He doesn’t seem to be saying no to anything.”

Of course, many former Obama aides are following the long-running Washington tradition of cashing in, but few have amassed as much of a cross section of earning power and political sway as Messina.

Messina declined to comment for this story, but he previously told POLITICO that he was only going to “work with people and causes that I believe in.” His allies say he’s remained true to that mission. They point to a thorough vetting process involving two top power lawyers he’s paying to screen and negotiate his deals — Obama attorney Bob Bauer and leading Washington deal maker Bob Barnett — and also say he clears anything potentially politically problematic with the White House.

While Messina is not required to disclose his private or foreign clients, his fingerprints are increasingly appearing all over the political and business worlds:

Obamaland

He chairs Organizing for Action, the nonprofit advocacy group pushing Obama’s agenda, which absorbed Obama’s reelection campaign committee and is hosting a dinner with Obama and Messina on Tuesday at Washington’s swank Mandarin Oriental hotel. Messina stayed on with the Obama campaign after 2012, helping it wind down and tending to the stewardship of its vaunted voter file. His recently ended management contract with the DNC, under which he helped select a new executive director and set up systems for utilizing key parts of the voter file, left a bad taste with some party loyalists, who wondered why the committee was paying a retainer to Messina while the party was saddled with debt.

Hillaryland

Messina is nurturing relationships with Clinton’s biggest donors, like Haim Saban, with whom he met this month in Los Angeles. Last month, he signed on to chair Priorities USA, the super PAC and 501(c)(4) nonprofit group that raised $85 million to boost Obama’s reelection campaign. The group has formally switched its allegiance from Obama to Clinton and is planning to raise even more to help Clinton in a hoped-for 2016 presidential run. Priorities is in the process of closing down the group’s nonprofit arm, which raised $11 million in undisclosed money in the 2012 cycle but never became a central part of the operation, and gave Republicans an opening to attack the group for raising the same sort of anonymous cash that Democrats bash.

Business

The Messina Group, a consulting firm he started last year, has been growing to accommodate its founder’s expanding corporate, nonprofit and political portfolios, becoming something of a hub between the disparate arms of Messina Inc. The American Gaming Association last month signed the firm to assist in its push to build support for online gambling. Yet both Priorities and OFA recently moved into the firm’s downtown Washington offices, which is set to host a meeting and cocktail reception Monday afternoon for OFA’s top staff and donors who contributed or raised $500,000 for the group. Priorities and OFA both pay rent to The Messina Group. And OFA pays Messina a retainer for his services, which Priorities is expected to start doing as well next year as it increasingly ramps up — under Messina’s direction — in preparation for the 2016 primaries.

Speaking gigs

A common ritual for high-profile politicians and operatives entering the private sector including Rove, this is where Messina pocketed some of his first big private-sector checks, earning payments “in the mid-five figure range” for each speech, according to the source close to him. In addition to API’s board of directors and the government of Sharjah, Messina has spoken to the Western Energy Institute, the National Association of Real Estate Investment Trusts, various health care groups and an oil-company sponsored conference in Azerbaijan. The source close to Messina cautioned not to conflate his business and political work with the speaking gigs, explaining that, just because he might give a talk “it doesn’t mean that Jim condones everything that any individual group has done or said or would do.” Sometimes, though, it all aligns perfectly, such as when he gave a speech to a venture capital firm run by a major Obama donor named Vinod Khosla, with whom he had become friendly. The CEO of a Khosla-backed green energy company called LanzaTech attended the speech and was impressed. In September, she asked him to join her board, and he accepted.

Corporate world

Messina this month joined GOP pollster Frank Luntz in accepting positions on the advisory board of a clean energy company called Opower. Both LanzaTech, which has been awarded at least $6.2 million in Energy Department grants, and Opower, whose founder boasts of meeting Obama in the White House and hosting him at the company’s suburban Washington headquarters, seem eager to expand their political footprints, making Messina a smart addition for them. Messina was tapped for the board posts — both of which come with stock options but no regular pay — because of his experience managing the 5,000-employee, $1 billion Obama campaign, the source said.

Data

Messina discussed joining the boards of Civis Analytics and BlueLabs, competing data firms started by employees of Obama’s campaign, before settling on taking only informal advisory roles with the firms. Both are said to be in the running for Priorities USA work, and Messina recommended them to the Florida donor Morgan, who said he’s considering hiring them for his business. BlueLabs has been paid by the DNC for data work, according to Federal Election Commission filings, while Civis — which is funded by Google Chairman Eric Schmidt, with whom Messina boasts of a close bond — has been paid by OFA for issue advocacy work, according to the group.

Campaign consulting

Messina is limiting his 2014 domestic campaign work to advising the Democratic gubernatorial candidates Charlie Crist of Florida and Anthony Brown of Maryland. He’s also followed the well-worn path of former top American political consultants who take their talents overseas, signing on to represent British Prime Minister David Cameron. He even had preliminary discussions with fellow Democratic presidential campaign veteran Paul Begala about the possibility of working for Ukrainian opposition leader and former world heavyweight boxing champion Vitali Klitschko. Begala has previously worked for Klitschko, and he approached Messina about signing on for a potential future election, but the source close to Messina said “Jim never met with Klitschko, never met with the people in his party,” and added “at this time, particularly with everything going on, it doesn’t look like it’s something that we’re going to explore.”

Concerns about possible conflicts regarding Messina’s work for his varied clients have been expressed on both sides of the Atlantic. He was criticized in the United Kingdom after agreeing to represent the American Gaming Association, since Cameron has expressed reservations about gambling in his country. The source close to Messina said, “Jim is not involved with [Cameron’s] policy development,” adding of The Messina Group, “We just do domestic gaming, so that’s different than what’s in the U.K.”

And some on the American left have taken issue with Messina’s work for Cameron, whose Conservative Party holds divergent views from Democrats on a number of hot-button issues like immigration and government spending. Messina’s U.K. work is an example of a contract that was cleared by the White House, two sources familiar with the matter said.

Messina boosters suggest that working in the unlimited money infrastructure — as opposed to in the White House, at the DNC or for a presidential candidate — affords him more flexibility.

“If you’re running a presidential campaign, you can’t do anything else, period,” said Begala, who after serving as chief strategist for Bill Clinton’s 1992 campaign, has had a long career as a pundit and political wise man. He was one of the earliest big-names to sign on with Priorities USA in 2011 and helped recruit Messina to the group as it was transitioning from Obama to Clinton after the election. “Now, running a super PAC is much different. Jim is one of several strategists, and we get plenty of his time and attention.”

Messina’s allies attribute the Democratic criticism to professional jealousy, and they reject the idea he’s motivated by money, suggesting he could make a lot more if he were to go the 100 percent corporate route.

Indeed, there’s little evidence that Messina has splurged in the year or so since he started reeling in private-sector paydays. He did take a two-week trip to Italy after Election Day with his fiancée during which he pledged to “become an expert on red wine,” and he used to drive a black Porsche convertible around Washington. But a public records search turned up no evidence of recent property purchases, and the only homes that could be found in his name were a pair of rental properties, one in Nampa, Idaho, and the other in Missoula, Mont., that he reported on a 2009 White House disclosure. Before the 2012 campaign, he sold for $425,000 a modest Maryland home that he had owned for about seven years.

Messina got his start in politics in 1993, when, as a senior at the University of Montana, he managed the reelection campaign of the mayor of Missoula. But he really found his political sweet spot a couple years later, when he was hired by Sen. Max Baucus, who brought Messina to Washington and became something of a father figure. After bouncing around the Hill and the campaign trail for more than a decade, Messina was recruited to join Obama’s 2008 campaign, and he followed Obama into the White House, earning a reputation as a fixer. He secretly brokered a deal with deep-pocketed special interests to advance Obamacare, but he also drew scorn from liberal activists who saw him as a heavy-handed enforcer driven more by pragmatism than ideology.

Unlike Rove, Messina did not re-enter the White House after his boss won reelection, instead beating a path directly to the private sector and big-money politics. His still-strong ties to the White House — which two Democrats said he used to push for Baucus to be tapped as ambassador to China — have helped him transition to his new role but also caused some problems.

The White House worried that Messina’s assuming leadership of Priorities USA could make it look as though Obama were giving his blessing to Clinton even as his own vice president, Joe Biden, is weighing a 2016 run. The Biden concern caused a lengthy delay in signing off on Messina officially joining Priorities, according to two people familiar with the deliberations.

In other ways, though, Messina’s experience makes him extremely well-suited to become the left’s leading big-money man and shadow party boss.

Messina earned the admiration of Bill Clinton, according to several sources familiar with their relationship, which goes a long way toward healing lingering animosity from the bitter 2008 Democratic primary between Hillary Clinton and Obama. Instead of viewing Messina with suspicion, a number of Clintonites believe he has acumen worth tapping.

Plus, Messina has “a good and deep relationship with the donors throughout the country,” said top Obama adviser David Plouffe. That includes Hollywood producer Jeffrey Katzenberg and time-share mogul Stephen Cloobeck, in addition to Google’s Schmidt, as well as Morgan, Khosla and others.

Plouffe, who ran Obama’s historic 2008 election and recruited Messina into Obamaland, did not work as assiduously to develop big-money ties . And, while he did draw some fire for his forays on the speaking circuit, he generally took a lower-profile than Messina in post-campaign life, as have most former Obama aides. But, Plouffe explained, Messina is “still hungry to stay involved in politics.”

His critics, though, contend he exaggerates his access to the president and his mastery of the data analytics for which the reelection campaign is known. Both themes figure prominently in Messina’s stock speech.

“I learned a very valuable lesson: never go for a swim in the Pacific Ocean with the president,” he warned a healthcare company, explaining that “there’s all these Navy Seals below him ready to catch him.” He highlights his ties to influential donors or executives like Schmidt (“my mentor on how to be a manager of several thousand people”) and Steven Spielberg (who told him “you’ve got to figure out how to be sexy … I don’t think you have any idea about that”). Touting his role in pioneering political technology, he told one group, “Big data is here forever. You guys all know what big data is? Data is now becoming persuasive in this world. We spent millions of dollars trying to figure out how to use data to make your lives easier.”

Messina’s speeches are arranged through The Harry Walker Agency, which also counts Rove as a client, and has offered them “as a powerful political duo” for debates in front of various companies and groups. The lone time they appear to have shared a stage, at the 2013 Chief Financial Officers and Tax Officers Summit in Las Vegas, things got rather heated. It was a “hard-hitting format” that “kept every participant on the edge of their seat until the closing bell,” recalled the conference organizer Marcus Evans.

Messina pointed out in a recent speech excerpted on the agency’s website that the job he held in the White House — deputy chief of staff — was “the job that Karl Rove had, it’s the job that Harold Ickes had, it’s the job that Josh Lyman on the West Wing had. And so I was convinced I would never leave that job.”

Rove declined to comment on the comparison between him and Messina.

But Fred Malek, an influential GOP financier who has worked closely with Rove over the years, suggested Messina should be flattered to be mentioned in the same breath as Rove as a political operative, and brushed off suggestions that Rove is a glory hound.

“With Rove it’s about the cause and the candidates and it’s regrettable that anyone would ascribe anything but noble motives to anybody who is going to spend their life in pursuit of a political cause,” Malek said.

Messina has taken evident glee in calling out Rove on his disastrous 2012, during which his Crossroads outside spending operation raised $325 million, mostly spent on negative ads that did not achieve their goal of defeating Obama or capturing the Senate. During a ticket-only event at which OFA was unveiled to big donors at Washington’s Newseum before Obama’s 2013 Inauguration, Messina swiped Rove over his electoral vote prediction of a Romney win. “I would like to point out Karl Rove was completely wrong, thank you,” Messina said to loud applause, according to a recording made by a POLITICO reporter who received a ticket from a donor. “I know — cheap shot, but I deserve it.”

Tactics and demeanor aside, the Florida donor Morgan said Messina and Rove have at least one thing in common.

“These guys like Jim Messina, they are junkies when it comes to politics — whether it’s Begala or Karl Rove — this is in their system, it’s in their DNA,” said Morgan. “This is what they do.”